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Year of first isolation: |
1967 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Morus sp [Moraceae] »  ![Wikipedia: Morus sp [Moraceae]](/images/wikipedia.png)
Achyranthes fauriei [Amaranthaceae] »
Polypodium vulgare [Polypodiaceae] »
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| Occurence in animals: |
Callinectes sapidus [Portunidae] »
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![INOKOSTERONE [= CALLINECDYSONE A]](images/ecdy/216.gif)
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| Canonical SMILES | CC(CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)CO | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | CC(CC[C@H]([C@@](C)([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)O)O)CO » 
CC(CCC([C@@](C)(C1CC[C@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(CC(C(C4)O)O)C)C)O)O)O)CO »
C[C@@H](CC[C@H]([C@@](C)([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)O)O)CO »
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,7-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 15130-85-5 | | PubChem CID | 5458789 | InChiKey
[ ChemIDPlus: search ] | JQNVCUBPURTQPQ-XDWLXSIGSA-N | | InChI | InChI=1S/C27H44O7/c1-15(14-28)5-6-23(32)26(4,33)22-8-10-27(34)17-11-19(29)18-12-20(30)21(31)13-24(18,2)16(17)7-9-25(22,27)3/h11,15-16,18,20-23,28,30-34H,5-10,12-14H2,1-4H3/t15?,16-,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 462 (M -18)+, 444, 426 (M- 3x18)+ , 411, 363, 345, 311, 126, 99, 81, 43 | | HR-MS | |
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| C5D5N | | (I) (II) | 25R+25S pure 25S | | 01 | 37.9 38.4 | | 02 | 68.0 68.6 | | 03 | 68.0 68.5 | | 04 | 32.2 32.6 | | 05 | 51.3 51.9 | | 06 | 203.3 204.1 | | 07 | 121.6 122.2 | | 08 | 165.9 166.7 | | 09 | 34.4 34.5 | | 10 | 38.6 39.2 | | 11 | 21.4 * 21.6 | | 12 | 31.7 $ 32.2 | | 13 | 48.1 48.6 | | 14 | 84.1 84.6 | | 15 | 32.0 $ 32.6 | | 16 | 21.6 * 22.0 | | 17 | 50.0 50.6 | | 18 | 17.8 18.4 | | 19 | 24.4 25.0 | | 20 | 76.7 77.3 | | 21 | 21.1 22.1 | | 22 | 77.2 77.4 77.7 | | 23 | 30.1 30.7 | | 24 | 31.7 32.0 32.6 | | 25 | 36.4 36.7 37.2 | | 26 | 67.3 68.0 67.8 | | 27 | 17.0 17.8 18.4 |
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| C5D5N | | (I), (II) | 25R+25S pure 25S | | 01-Ha | 1.91 | | 01-Hb | 2.18 (dd, 3.7, 14) | | 02-Ha | 4.20 (m, w1/2 = 22) | | 03-He | 4.26 (m, w1/2 = 8) | | 04-Ha | 1.80 | | 04-He | 2.05 | | 05-H | 3.05 (dd, 3.2, 12.9) | | 07-H | 6.28 (d, 2.5) | | 09-Ha | 3.62 (m, w1/2= 22) | | 11-Ha | 1.75 | | 11-He | 1.90 | | 12-Ha | 2.62 (ddd, 5, 13, 13) | | 12-He | 2.05 | | 15-Ha | 2.10 | | 15-Hb | 1.85 | | 16-Ha | 2.48 | | 16-Hb | 2.05 | | 17-H | 2.98 (t, 9.4) | | 18-Me | 1.19 (s ) 1.25 (s ) | | 19-Me | 1.07 (s ) 1.10 (s ) | | 21-Me | 1.52 (s ) 1.60 (s ) | | 22-H | 3.87 (brd, 1.4, 10.7) | | 23-Ha | 1.85 | | 23-Hb | 2.14 | | 24-Ha | 2.25 | | 24-Hb | 1.48 | | 25-H | 1.83 | | 26-Ha | 3.81 (dd, 5.5, 10.4) | | 26-Hb | 3.69 (dd, 6.4, 10.3) | | 27-Me | 1.03 (d, 6) 1.08 (s ) |
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| M.P. | 255 °C (decomp.) | | [α]D27 | + 59.4 ° (c 0.78; MeOH) | | IR (KBr) ν max (cm-1) | 3400 (OH), 1645 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 243 (4.084) |
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| HPTLC | | | TLC | NP-TLC on silica gel : Rf 0.17 (CHCl3/EtOH 4:1); RP-TLC : Rf 0.47 (C18 bonded silica gel MeOH/H2O 65:35; Rf 0.49 (paraffin coated silica gel MeOH/H2O 50:50) | | GLC | Rt of 8 min on 1.5% OV101 (0.9 m x 4 mm i.d. at 285°C) following silylation for 60 h at 140°C (ecdysone : 5.85 min). | | HPLC | Ret 22.8 and 25.0 min (2 isomers) (20E : 18.1 min) (column Zorbax C8, 250 mm x 4.6 mm i.d., solvent ACN/H2O 12:88, flow-rate 2 ml.min-1) |
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Drosophila melanogaster BII cell assay: EC50 = 1.1 x 10-7M (25R/25S) | Drosophila melanogaster BII cell assay: EC50 = 1.5 x 10-7M (25R); EC50 = 2.7 x 10-7M (25S) | Calliphora vicina imaginal disc assay: EC50 = 1.5 x 10-7M | Drosophila melanogaster imaginal disc assay: EC50 = 4.5 x 10-7M | Drosophila melanogaster Kc-H cell assay: EC50 = 1.3 x 10-7M | Calliphora assay: 100% (20-hydroxyecdysone = 100%) |
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| First isolation | TAKEMOTO, T. et al. (1967) Yakugaku Zasshi 87, 325-327 |
 | | General | TAKEMOTO, T. et al. (1967) Yakugaku Zasshi 87, 748 |
| | General | TAKEMOTO, T. et al. (1967) Yakugaku Zasshi 87, 1469-1473 |
| | General | TAKEMOTO, T. et al. (1967) Yakugaku Zasshi 87, 1474-1477 |
| | General | FAUX, A. et al. (1969) Chem. Commun., 175-176 |
| | Bioactivities | CHIHARA, C.J. et al. (1972) J. Insect Physiol. 18, 1115-1123 |
| | General | HIKINO, H. et al. (1976) Tetrahedron 32, 3015-3021 |
| | Bioactivities | CHERBAS, L. et al. (1980) W. Roux Arch. Devel. Biol. 189, 1-15 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | WILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 |
| | General | BIELBY, C.R. et al. (1986) J. Chromatogr. 351, 57-64 |
| | Bioactivities | CLEMENT, C.Y. et al. (1993) Insect Biochem. Molec. Biol. 23, 187-193 |
| | Bioactivities | TERENTIOU, P. et al. (1993) Insect Biochem. Molec. Biol. 23, 131-136 |
| | Identification | COLL, J. et al. (1994) Tetrahedron 50, 7247-7252 |
| | Bioactivities | DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 |
| | Synthesis | YINGYONGNARONGKUL, B.-E. et al. (2000) ScienceAsia 26, 15-20 |
| | Synthesis | YINGYONGNARONGKUL, B.-E. et al. (2005) Steroids 70, 636-644 |
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Permanent link to this datasheet: INOKOSTERONE [= CALLINECDYSONE A]
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